Formic Acid → 1-(5-Methyl-[1,3,4]oxadiazol-2-yl)-piperidin-4-one

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Reaction Steps

4-Hydroxy-1-(5-methyl-[1,3,4]oxadiazol-2-yl)-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid allyl ester potassium salt (163 mg, 0.54 mmol) was dissolved in little 25% aqueous HCl solution and the solvent was removed under reduced pressure. The residue was evaporated twice with toluene/tetrahydrofurane. The residue was suspended in tetrahydrofurane (0.26 mL). To a solution of triethyl amine (263 L, 1.88 mmol) and formic acid (42 L, 1.08 mmol) in tetrahydrofurane (0.51 mL) was added under nitrogen and stirring a solution of palladium (II) acetate (3.0 mg, 0.013 mmol) and triphenylphosphine (7.3 mg, 0.027 mmol) in tetrahydrofurane (0.77 mL). After stirring for 5 minutes at room temperature the prepared catalyst solution was added to the suspension. The reaction was stirred at room temperature for 1 hour, poured onto water and extracted twice with ethyl acetate. The combined organic layers were washed with saturated aqueous NaCl solution, dried over sodium sulfate, filtered and the solvent was evaporated under reduced pressure. The title compound was obtained as a yellow viscous oil (54 mg, 55%).

Provenance & Evidence